About us
🎉 Welcome to & Windy City Wanderers! 🌆
We’re so glad you’re here!
Whether you’re new to Chicago or a lifelong local, these sister groups are all about being a tourist in your own city—discovering hidden gems, rich history, fun facts, and unforgettable experiences across Chicagoland. 🗺️✨
Windy City Wanderers is the sister group to 1001 Things to See in Chicago Before You Die, and we host many joint events together—so you’ll often see crossover adventures and shared outings. 🤝
***
🗓 What to Expect
We host fun, social outings year-round (yes, even in winter ❄️). Expect:
• Walking tours & neighborhood explorations
• Concerts, lectures & theater
• Pop-up dinners, trivia & social nights
• Museums, festivals & special events
Events take place throughout Chicago and nearby suburbs like Evanston, Oak Park, and Park Ridge.
🚇 All events are CTA-accessible.
***
💬 Why Join?
• Discover new places all over Chicagoland
• Meet new people and make real connections
• Enjoy an active, well-curated event calendar
• Try the group FREE for 90 days
***
💰 Membership
• 90-day free trial
• Annual dues: $12/year after the trial
• 🎉 Host an event and your dues are waived!
***
🚨 RSVP / No-Show Policy (Please Read)
To keep events fair and running smoothly:
• A no-show without updating your RSVP = 1 strike
• 3 strikes = a 3-month pause from events
***
🤝 Stay Connected
📘 Facebook Page
https://www.facebook.com/profile.php?id=61576822533554
👥 Facebook Group
https://www.facebook.com/groups/1571684466442303
📸 Instagram
https://www.instagram.com/1001thingstoseeinchicago/
🌬️ !001 Things to See in Chicago Before You Die Meetup (sister group)
https://www.meetup.com/windy-city-wanderers
***
💡 Have an idea for an event? Want to host or co-host?
Just message me—I’d love to hear from you!
Can’t wait to explore, wander, and discover Chicago together 💙
Cheers,
Giovina Romandine
Organizer, Windy City Wanderers 🌬️🚶♀️🚶♂️
Featured event
🎨🖼️ 79 Years & Still the Best — 57th Street Art Fair in Hyde Park! 🎶✨
🎨🖼️ 79 Years & Still the Best — 57th Street Art Fair in Hyde Park! 🎶✨
79th Annual 57th Street Art Fair — Hyde Park! (Part 2 of 2)
🎨 IT'S BACK — Chicago's Oldest & Best Art Fair! The 79th Annual 57th Street Art Fair is one of the finest FREE art fairs in the city and a beloved Hyde Park tradition! Kick off summer at the first major art fair of the season, located in the beautiful Hyde Park neighborhood on the South Side — adjacent to the University of Chicago campus and the former home of President Barack Obama. 🏛️
Browse the work of 200 exhibitors — paintings, ceramics, jewelry, glasswork & more — while enjoying live Blues music at the Buddy Guy's Legends Stage! 🎸 Whether you're a seasoned collector or new to the art scene, this is THE place to buy art. All artists are stationed in their booths throughout the weekend to discuss their work. 🖌️
📅 Saturday, June 6, 2026
⏰ 11:45 AM – 2:30 PM
📍 Meet at William H. Ray Elementary School 5631 S. Kimbark Ave, Chicago, IL 60637 (Look for the sign that says "Ray Elementary School" — right in the middle of the fair!)
🍳 Did you sign up for Brunch first? Join us for Part 1 — Breakfast at Roux Diner before the fair! 👉 https://www.meetup.com/windy-city-wanderers/events/307080309/
***
🗓️ Tentative Itinerary:
🍳 9:45–11:30 AM — Breakfast at Roux Diner (Part 1 — sign up separately!)
👋 11:45–11:55 AM — Meet & greet outside Ray Elementary School
🎨 11:55 AM–2:30 PM — Break into small groups of 4–5 & wander the fair!
🚉 2:30 PM — Regroup at Ray Elementary for those taking the Metra home
⚠️ Check back for updates to the above schedule!
***
🏛️ A Little History The 57th Street Art Fair is the oldest juried art fair in the Midwest, founded in 1948 by silversmith artist Mary Louise Womer. Her studio, The Little Gallery, was a local gathering spot for artists who came to talk and drink tea. Wanting to showcase local art to the community, she took to the streets — literally stringing wires from trees and fences along 57th Street for artists to hang their work. Fifty-one artists, many from the Art Institute and Institute of Design, each paid 50 cents to participate. By Sunday night, earnings totaled $500 — and Womer and her husband cleaned up themselves! 🎨✨
***
🔗 Fair Info & Maps:
🌐 http://www.57thstreetartfair.org/general-information
🗺️ https://www.57thstreetartfair.org/2017-map--legend (check back for updates)
🚗 https://www.57thstreetartfair.org/parking--directions (check back for updates)
***
🚗 Parking & Transit:
⚠️ Parking is very limited during the fair — public transit strongly recommended!
🚇 Metra Electric trains run near the fair
🚌 Several CTA bus routes nearby
📱 SpotHero or ParkingWiz for cheapest & safest parking options 🔗 CTA Trip Planner: https://www.transitchicago.com/planatrip/
📞 Lost or late? Call (312) 835-4259 The school building is open during the fair — meet outside by the Ray Elementary sign!
***
📌 NO-SHOW POLICY:
❗ 3 no-shows without updating your RSVP = 3-month freeze from future events
⏰ Update your RSVP by event start time — after that, message the host directly
✅ Check in with the host upon arrival (required for walks, tours & festival events)
🚫 Continual no-shows may result in removal from the group
Art, music, sunshine & good company — see you in Hyde Park! 🎨🌞🎶
Upcoming events
32
🌊👟 Lace Up! Lakefront Stroll: Oak Street to Diversey + Lunch! 🍕🦅
Whispers at Oak Street Beach, 1001 N. Lake Shore Drive, chicago, IL, US🌊👟 Lace Up! Lakefront Stroll: Oak Street to Diversey + Lunch! 🍕🦅
Lakefront Trail Walk: Oak Street Beach to Diversey Harbor + Lunch!
☀️ Our Friday Afternoon Walks Are Back! I have Summer Fridays, so all summer long we'll be doing leisurely walks across Chicago — and this is our first one! 🎉
📅 Friday, June 5, 2026
⏰ 3:00 PM – 7:00 PM
📍 START: Whispers at Oak Street Beach 1001 N Lake Shore Dr, Chicago, IL 60611
🍽️ END: Bacino's Italian Grill 248 W Diversey Pkwy, Chicago, IL 60657
⚠️ IMPORTANT: THIS IS A ONE-WAY WALK! We start at Oak Street Beach and end ~2.6 miles north at Diversey Harbor. We do NOT return to the start! If you drive, plan ahead — park at Diversey, in the middle of the route, or be prepared to bus or walk back to your car.🗺️ About the Walk We'll stroll one of Chicago's most beautiful stretches of the iconic 18-mile Lakefront Trail — a paved path hugging the Lake Michigan shoreline. The 2018 trail separation project divided it into dedicated bike and pedestrian paths for a safer, more enjoyable experience. 🚴♀️🚶♀️
📍 Highlights Along the Way:
🏖️ Oak Street Beach
🏖️ North Ave Beach
🌊 South Lagoon
🏖️ Fullerton Beach
🎭 Theater on the Lake
🌀 Ten Thousand Ripples
🗿 Emanuel Swedenborg Monument
🎾 Lincoln Park Tennis Association
⛳ Diversey Driving Range & Mini Golf
🌱 Diversey Harbor Community Garden
⚓ Diversey Harbor🍽️ After the Walk — Lunch at Bacino's Italian Grill! Join us for a bite at Bacino's Italian Grill, a cute spot with great food right at Diversey Harbor, next to the Driving Range & Mini Golf. 🍕🥗
📍 248 W Diversey Pkwy, Chicago, IL 60657 🌐 https://www.bacinositaliangrill.com🎒 What to Bring:
💧 Water
☀️ Sunscreen
🧴 Hand sanitizer
👟 Good walking shoes 👗
Dress for summer weather in Chicago!🚻 Restroom note: Facilities along the trail are limited — please plan accordingly!
📍 WHERE TO MEET: Meet outside Whispers at Oak Street Beach. There is a path around the Drake Hotel to get from the bus stop to the Lakefront Trail. Look for beach signs or use GPS on walk mode.
🚗 Parking Tips:
Street parking at Oak Street Beach is very limited & expensive. Best options:
🅿️ Park at Diversey Harbor (end of route)
🅿️ Park somewhere in the middle
📱 Use SpotHero or ParkingWiz for nearby lots🚌 Transit: Check Google Maps, CTA Trip Planner, or the CTA website for directions to Oak Street Beach. 🔗 https://www.transitchicago.com/planatrip/
🔗 https://www.chicagoparkdistrict.com/parks-facilities/lakefront-trail
📞 Lost or late? Call (312) 835-4259
📌 NO-SHOW POLICY:
❗ 3 no-shows without updating your RSVP = 3-month freeze from signing up for future events
⏰ Update your RSVP by event start time — after that, message the host directly
✅ Check in with the host upon arrival (required for walks, tours & festival events)Lace up those shoes — Chicago's lakefront is calling! 🌊🌅
18 attendees
🧘♀️ Mat & Morning Magic: Free Yoga in the Park! 🌞
Millennium Park, 201 E Randolph St, Chicago, IL, US🧘♀️ Mat & Morning Magic: Free Yoga in the Park! 🌞
🌞 Millennium Park Outdoor Yoga – Hosted by Carol
Stretch, smile, and salute the sun with your fellow yogis on the Great Lawn — Carol's got her purple mat and good vibes ready!
🧘♀️ FREE Summer Workout Series
📍 Millennium Park – Great Lawn (Behind Harris Theater)
📅 Saturday, June 6, 2026
🕘 Yoga: 9:00 AM – 9:45 AM | Meet at 8:40 AM!Join your event host Carol for the kickoff to the Millennium Park Summer Workouts! She'll be at the front of the lawn area near the stage with her purple yoga mat so you can easily find her. Enter the park from Michigan Ave at Washington or Madison.
***
💧 Bring:
🧘♀️ Yoga mat
💦 Water bottle
☀️ Sunscreen
👗 Comfortable clothes for movement***
🗓️ Full Workout Schedule:
8:00–8:45 AM — Pilates (Carol won't be here for this, but you can join!)
9:00–9:45 AM — Yoga *(Our group joins here!)*⭐
10:00–10:45 AM — Cardio Kickboxing
11:00–11:45 AM — Zumba***
🟢 Weather Note: Event will be canceled if it rains.
⚠️ Check back weekly — Carol decides week-to-week whether she's hosting, so RSVP accordingly!
📌 CHECK IN WITH CAROL upon arrival so she knows you're there! She'll post what she's wearing — look for the purple yoga mat up front! 💜
Leave comment if cannot find the group!***
🔗 More Info: 🌐 https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park4.html
🌐 https://millenniumparkfoundation.org/programs/summer-workouts/***
📌 NO-SHOW POLICY:
❗ 3 no-shows without updating your RSVP = 3-month pause from signing up
⏰ Update your RSVP before event start time
✅ Must check in with host upon arrival — failure to do so counts as a no-show
🚫 Repeated no-shows = removal from the groupCome move, stretch & soak up summer in the city with us! 🌿🌞
2 attendees
🍳🎨 Beignets & Brushstrokes — Roux Diner Before the Art Fair! 🥐☕
Roux, 1055 E 55th Street, Chicago, IL, US🍳🎨 Beignets & Brushstrokes — Roux Diner Before the Art Fair! 🥐☕
Breakfast at Roux Diner — Before the 57th Street Art Fair! (Part 1 of 2)
📅 Saturday, June 6, 2026
⏰ 9:45 AM – 11:30 AM
📍 Roux Diner | 1055 E 55th St, Chicago, IL 60615 (Next to the University of Chicago in the heart of Hyde Park!)🎨 This is Part 1 of 2! Brunch first, then we walk 5 blocks to the 57th Street Art Fair! 👉 Sign up for Part 2 separately here: https://www.meetup.com/windy-city-wanderers/events/307080580/
***
🍴 About Roux Diner Chef Charlie McKenna's New Orleans-inspired, all-day breakfast spot in the heart of Hyde Park. Think beignets, shrimp & grits, Southern staples, great coffee — all in a stylish setting with retro accents. 🎷🥞
Several of our Hyde Park members rave about this place — best Southern breakfast in the area! I've been here several times and absolutely love it! 🙌
🔗 https://rouxdiner.com
📘 https://www.facebook.com/rouxdiner 🍽️ Menu: https://rouxdiner.com/menu***
⚠️ IMPORTANT NOTES:
🪑 No reservations — first come, first served seating
👥 Only 4–6 people per table — we may not all sit together 💳 Counter service — everyone pays on their own!
✅ Cash & credit both accepted
💝 Please tip your servers!***
🚨 IF ROUX IS TOO PACKED, we'll head to one of these nearby spots:
☕ Fairgrounds Coffee & Tea — 5500 S University Ave, Chicago, IL 60637
☕ True North Cafe Hyde Park — 1323 E 57th St, Chicago, IL 60637
🍕 Medici On 57th — 1327 E 57th St, Chicago, IL 60637
I'll post updates here if we move locations!***
🗺️ Getting to the Art Fair After Brunch: The 57th Street Art Fair is about 5 blocks from Roux — an easy walk to burn off breakfast! 🚶♀️🎨
🚗 Driving? Park in the middle between the restaurant and fair so you don't have to move your car twice!***
🚗 Parking & Transit:
🅿️ Metered parking on 55th Street
🅿️ Free parking on side streets
🚇 Metra Electric trains run near the fair
🚌 Several CTA bus routes nearby
📱 SpotHero or ParkingWiz for cheapest & safest options🔗 CTA Trip Planner: https://www.transitchicago.com/planatrip/
📞 Lost or late? Call (312) 835-4259
***
📌 NO-SHOW POLICY:
❗ 3 no-shows without updating your RSVP = 3-month freeze from future events
⏰ Update your RSVP by event start time — after that, message the host directly
✅ Check in with the host upon arrival (required for walks, tours & festival events)
🚫 Continual no-shows may result in removal from the groupSee you at Roux — beignets and good company await! 🍩☕🎨
7 attendees🎨🖼️ 79 Years & Still the Best — 57th Street Art Fair in Hyde Park! 🎶✨
William H. Ray Elementary School, 5631 S Kimbark Ave, Chicago, IL, US🎨🖼️ 79 Years & Still the Best — 57th Street Art Fair in Hyde Park! 🎶✨
79th Annual 57th Street Art Fair — Hyde Park! (Part 2 of 2)
🎨 IT'S BACK — Chicago's Oldest & Best Art Fair! The 79th Annual 57th Street Art Fair is one of the finest FREE art fairs in the city and a beloved Hyde Park tradition! Kick off summer at the first major art fair of the season, located in the beautiful Hyde Park neighborhood on the South Side — adjacent to the University of Chicago campus and the former home of President Barack Obama. 🏛️
Browse the work of 200 exhibitors — paintings, ceramics, jewelry, glasswork & more — while enjoying live Blues music at the Buddy Guy's Legends Stage! 🎸 Whether you're a seasoned collector or new to the art scene, this is THE place to buy art. All artists are stationed in their booths throughout the weekend to discuss their work. 🖌️
📅 Saturday, June 6, 2026
⏰ 11:45 AM – 2:30 PM
📍 Meet at William H. Ray Elementary School 5631 S. Kimbark Ave, Chicago, IL 60637 (Look for the sign that says "Ray Elementary School" — right in the middle of the fair!)🍳 Did you sign up for Brunch first? Join us for Part 1 — Breakfast at Roux Diner before the fair! 👉 https://www.meetup.com/windy-city-wanderers/events/307080309/
***
🗓️ Tentative Itinerary:
🍳 9:45–11:30 AM — Breakfast at Roux Diner (Part 1 — sign up separately!)
👋 11:45–11:55 AM — Meet & greet outside Ray Elementary School
🎨 11:55 AM–2:30 PM — Break into small groups of 4–5 & wander the fair!
🚉 2:30 PM — Regroup at Ray Elementary for those taking the Metra home⚠️ Check back for updates to the above schedule!
***
🏛️ A Little History The 57th Street Art Fair is the oldest juried art fair in the Midwest, founded in 1948 by silversmith artist Mary Louise Womer. Her studio, The Little Gallery, was a local gathering spot for artists who came to talk and drink tea. Wanting to showcase local art to the community, she took to the streets — literally stringing wires from trees and fences along 57th Street for artists to hang their work. Fifty-one artists, many from the Art Institute and Institute of Design, each paid 50 cents to participate. By Sunday night, earnings totaled $500 — and Womer and her husband cleaned up themselves! 🎨✨
***
🔗 Fair Info & Maps:
🌐 http://www.57thstreetartfair.org/general-information
🗺️ https://www.57thstreetartfair.org/2017-map--legend (check back for updates)
🚗 https://www.57thstreetartfair.org/parking--directions (check back for updates)***
🚗 Parking & Transit:
⚠️ Parking is very limited during the fair — public transit strongly recommended!
🚇 Metra Electric trains run near the fair
🚌 Several CTA bus routes nearby
📱 SpotHero or ParkingWiz for cheapest & safest parking options 🔗 CTA Trip Planner: https://www.transitchicago.com/planatrip/📞 Lost or late? Call (312) 835-4259 The school building is open during the fair — meet outside by the Ray Elementary sign!
***
📌 NO-SHOW POLICY:
❗ 3 no-shows without updating your RSVP = 3-month freeze from future events
⏰ Update your RSVP by event start time — after that, message the host directly
✅ Check in with the host upon arrival (required for walks, tours & festival events)
🚫 Continual no-shows may result in removal from the groupArt, music, sunshine & good company — see you in Hyde Park! 🎨🌞🎶
8 attendees
Past events
950
Group links
Members
186
